Cheap flights from Canada to Chicago

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Economy
Boston (BOS)
Chicago (CHI)
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How to find the cheapest flight from
Canada to Chicago (CHI)

All the information you need to plan the best null to CHI flight in 2022: compare Canada to Chicago flight prices with the expected peak season, weather and rainfall in Chicago.
What is the cheapest month to fly from Canada to Chicago?

Flights from Canada to Chicago lean towards being more expensive in October. Prices are generally better when you fly from Canada to Chicago in June, with the cheapest ticket starting at C$ 222.

How far in advance should I book a flight from Canada to Chicago?

Users have found that booking a flight from Canada to Chicago at least 44 days early can save you up to 47% on average compared to booking a flight this week. If booking 44 days before your flight isn’t an option for you, users have found flights from Canada to Chicago for as little as C$ 424 when booking for a departure date within the next two weeks. You can also check prices now. Some users have found airline tickets as low as C$ 526 for flights departing within the next 3 days.

When is the cheapest time to fly from Canada to Chicago (CA - CHI)?

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Canada to Chicago as you normally would.

Cheap flights from Canada to Chicago in September, October 2022

The best prices found for Canada to CHI flights for September, October
13 Oct - 17 Oct
C$ 234pp
YTZ
Toronto Island
Porter Airlines
Direct
MDW
Chicago Midway
MDW
Chicago Midway
Porter Airlines
Direct
YTZ
Toronto Island
15 Oct - 18 Oct
C$ 236pp
YTZ
Toronto Island
Porter Airlines
Direct
MDW
Chicago Midway
MDW
Chicago Midway
Porter Airlines
Direct
YTZ
Toronto Island
28 Oct - 8 Nov
C$ 237pp
YTZ
Toronto Island
Porter Airlines
Direct
MDW
Chicago Midway
MDW
Chicago Midway
Porter Airlines
Direct
YTZ
Toronto Island

Canada to Chicago 2022 flight deals

Cheap flights to Chicago from Canada found for this year
10 Nov - 15 Nov
C$ 225pp
YTZ
Toronto Island
Air Canada
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Air Canada
 
1 STOP
YTZ
Toronto Island
10 Nov - 15 Nov
C$ 226pp
YYZ
Toronto Pearson Intl
Air Canada
Direct
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Air Canada
Direct
YYZ
Toronto Pearson Intl
13 Oct - 17 Oct
C$ 234pp
YTZ
Toronto Island
Porter Airlines
Direct
MDW
Chicago Midway
MDW
Chicago Midway
Porter Airlines
Direct
YTZ
Toronto Island

Cheap Air Canada flights from Canada to Chicago

10 Nov - 15 Nov
C$ 225pp
YTZ
Toronto Island
Air Canada
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Air Canada
 
1 STOP
YTZ
Toronto Island
20 Oct - 26 Oct
C$ 243pp
YYZ
Toronto Pearson Intl
Air Canada
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Air Canada
 
1 STOP
YYZ
Toronto Pearson Intl
1 Nov - 8 Nov
C$ 247pp
YYZ
Toronto Pearson Intl
Air Canada
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Air Canada
 
1 STOP
YYZ
Toronto Pearson Intl

Cheap American Airlines flights from Canada to Chicago

30 Oct - 31 Oct
C$ 259pp
YYZ
Toronto Pearson Intl
American Airlines
Direct
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
Direct
YYZ
Toronto Pearson Intl
11 Nov - 13 Nov
C$ 275pp
YYZ
Toronto Pearson Intl
American Airlines
 
1 STOP
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
Direct
YYZ
Toronto Pearson Intl
14 Nov - 21 Nov
C$ 297pp
YYZ
Toronto Pearson Intl
American Airlines
   
2 STOPS
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
American Airlines
   
2 STOPS
YYZ
Toronto Pearson Intl

Direct flights to Chicago from Canada

Save time with Canada to Chicago direct flight deals
10 Nov - 15 Nov
C$ 226pp
YYZ
Toronto Pearson Intl
Air Canada
Direct
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Air Canada
Direct
YYZ
Toronto Pearson Intl
13 Oct - 17 Oct
C$ 234pp
YTZ
Toronto Island
Porter Airlines
Direct
MDW
Chicago Midway
MDW
Chicago Midway
Porter Airlines
Direct
YTZ
Toronto Island
15 Oct - 18 Oct
C$ 236pp
YTZ
Toronto Island
Porter Airlines
Direct
MDW
Chicago Midway
MDW
Chicago Midway
Porter Airlines
Direct
YTZ
Toronto Island

Last minute flights from Canada to Chicago

Late deals on round-trip flights to Chicago from Canada, departing today and this week
5 Oct - 9 Oct
C$ 249pp
YTZ
Toronto Island
Porter Airlines
Direct
MDW
Chicago Midway
MDW
Chicago Midway
Porter Airlines
Direct
YTZ
Toronto Island
4 Oct - 9 Oct
C$ 255pp
YYZ
Toronto Pearson Intl
Air Canada
Direct
ORD
Chicago O'Hare Intl
ORD
Chicago O'Hare Intl
Air Canada
Direct
YYZ
Toronto Pearson Intl
8 Oct - 9 Oct
C$ 265pp
YTZ
Toronto Island
Porter Airlines
Direct
MDW
Chicago Midway
MDW
Chicago Midway
Porter Airlines
Direct
YTZ
Toronto Island

One-way flights to Chicago from Canada

The cheapest one-way flights from Canada to Chicago
11:35 a.m. - 12:26 p.m.
WestJet
Direct
1h 51m
YYZ - ORD
WestJet
C$ 155
WestJet
3:00 a.m. - 4:05 a.m.
United Airlines
Direct
2h 05m
YYZ - ORD
United Airlines
C$ 158
United
7:20 a.m. - 1:55 p.m.
Air Canada
1 stop
7h 35m
YTZ - ORD
Air Canada
C$ 159
Travel2Be

Related info for your journey

Useful info, stats and facts about <span class="emphasized">Canada</span> to <span class="emphasized">Chicago</span> flights.

Flight FAQs

From Canada to Chicago

Which airlines flying from Canada to Chicago have flexible cancellations due to COVID-19?

Some of our airline partners flying from Canada to Chicago have new flexible policies in place due to COVID-19. Air Canada, American Airlines, and United Airlines are some of the carriers where you may find flexible cancellation policies. You can use our site to filter for airlines like Air Canada with this kind of flexibility.

Can I find flights from Canada to Chicago for under C$ 300 on Cheapflights?

Yes, there are multiple flights from Canada to Chicago for under C$ 300. The cheapest flight booked recently is on Air Canada for just C$ 225, but on average you can expect to pay C$ 245.

Are there direct flights from Canada to Chicago for under C$ 300 on Cheapflights?

Cheapflights has 20 direct flights from Canada to Chicago under C$ 300. A good price for a direct flight from Canada to Chicago is less than C$ 248.

Are there last-minute flights available from Canada to Chicago for under C$ 300?

There are currently 20+ open flights from Canada to Chicago within the next 7 days for less than C$ 300.

What days are direct flights available from Canada to Chicago?

You can find direct flights on the following days: Sunday, Monday, Wednesday, Thursday, Friday, Saturday.

How many flights depart from Canada to Chicago on average per day?

6 flight departures from Canada to Chicago per day on average.
Afternoon (Noon - 6pm) - 83% of flight departures
Evening (6pm - Midnight) - 17% of flight departures

How long is the flight from Canada to Chicago?

A quick flight from Canada to Chicago can take about 1h 50m. Air Canada provides one of the quickest options available for as low as C$ 225. Canada and Chicago are separated by a distance of 703 km. When browsing for deals, the options you’ll see will be for both direct flights and flights with stops.

What are the cheapest airlines to fly from Canada to Chicago one-way?

To fly one-way, consider booking your trip with Air Canada, which is currently one of the cheapest options available, starting at C$ 134. Porter Airlines flights start at C$ 144 while deals on WestJet start at C$ 155 one-way.

What are the most popular routes from Canada to Chicago?

When deciding which route to take from Canada to Chicago consider Toronto Pearson Intl - Chicago O'Hare Intl, Montreal Pierre Elliott Trudeau Intl - Chicago O'Hare Intl or Toronto Island - Chicago Midway as they are the most popular.

What are the most reliable airlines from Canada to Chicago?

Before booking your flight to Chicago from Canada, check out the most reliable airlines to get you to your destination on time: ANA (88%), Air Wisconsin (82%), Copa Airlines( 82%).

What are the cheapest flights from Canada to Chicago?

Looking at all options, your cheapest flight can be booked for C$ 211. While the most popular route (Toronto Pearson Intl - Chicago O'Hare Intl) can be booked for C$ 256 on average our data indicates C$ 1,853 when flying from Canada to Chicago.

What are the most popular airlines that fly from Canada to Chicago?

Undisclosed Carrier, American Airlines and Air Canada are the most popular airlines when flying from Canada to Chicago.

COVID Restrictions

View COVID Travel Restrictions for Chicago, IL

Do I need a COVID test to fly to Chicago from Canada?

Information is based on travel restrictions from Canada to Chicago

Most visitors from Canada need to provide a negative COVID-19 test result and/or quarantine to enter Chicago.

COVID-19 testing requirements
Visitors from Canada are not required to present a negative COVID-19 PCR test or antigen result upon entering Chicago.

Quarantine requirements
Visitors from Canada are not required to quarantine after entering Chicago.

Do I need a test to fly back to Canada from Chicago?

Returning to Canada from Chicago

COVID-19 testing requirements
Visitors from Chicago must present a negative RT-PCR (NAAT) or Antigen (quick-test) test taken 72 hours for RT-PCR (NAAT) and 1 day for Antigen (quick-test) before departing to Canada.

Quarantine requirements
Visitors from Chicago are not required to quarantine after entering Canada.

Hide COVID Travel Restrictions for Chicago, IL

Departure points for flights from Canada to Chicago

Select to see more specific information for flights to Chicago from all departure points in Canada.

Top 10 airlines flying from Canada to Chicago

The chart below displays the airlines Cheapflights users travelling from Canada to Chicago choose most often. Cheapest and average prices are based on aggregated data from the past 12 months.
Airline Cheapest Average Flexibility On-time COVID-19 safety
Juneyao Airlines
C$ 27 C$ 42 No cancel fee 66%

We couldn't confirm the COVID-19 safety measures taken by Juneyao Airlines. Please check directly on their website for additional information.

Search Juneyao Airlines flights
WestJet
C$ 131 C$ 515 No cancel fee 60%
Search WestJet flights
Delta
C$ 170 C$ 558 No cancel fee N/A
Search Delta flights
Swoop
C$ 175 C$ 190 No cancel fee N/A
Search Swoop flights
Flair Airlines
C$ 182 C$ 244 No cancel fee N/A
Search Flair Airlines flights
Endeavor Airlines
C$ 196 C$ 818 No cancel fee N/A

We couldn't confirm the COVID-19 safety measures taken by Endeavor Airlines. Please check directly on their website for additional information.

Search Endeavor Airlines flights
Air Canada
C$ 234 C$ 602 No cancel fee 67%
Search Air Canada flights
Frontier
C$ 249 C$ 368 No cancel fee 62%
Search Frontier flights
Porter Airlines
C$ 256 C$ 372 No cancel fee 52%
Search Porter Airlines flights
United Airlines
C$ 265 C$ 656 No cancel fee 69%
Search United Airlines flights
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